US7408085B2 - Rapid cost effective method for the synthesis of TPD-type arylamines - Google Patents
Rapid cost effective method for the synthesis of TPD-type arylamines Download PDFInfo
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- US7408085B2 US7408085B2 US11/563,937 US56393706A US7408085B2 US 7408085 B2 US7408085 B2 US 7408085B2 US 56393706 A US56393706 A US 56393706A US 7408085 B2 US7408085 B2 US 7408085B2
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- compound
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- carbon atoms
- aryl
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- 238000000034 method Methods 0.000 title claims abstract description 67
- 150000004982 aromatic amines Chemical class 0.000 title description 16
- 230000015572 biosynthetic process Effects 0.000 title description 10
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 230000008569 process Effects 0.000 claims abstract description 55
- -1 dibromobiphenyl compound Chemical class 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 40
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 6
- DSYQHWPNJZFRCU-UHFFFAOYSA-N 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane Chemical compound C1C(P2)(C)OC3(C)CC2(C)OC1(C)O3 DSYQHWPNJZFRCU-UHFFFAOYSA-N 0.000 claims description 5
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- FTDZECHQBVIHKZ-UHFFFAOYSA-N 5,5-dibromo-2-phenylcyclohexa-1,3-diene Chemical group C1=CC(Br)(Br)CC=C1C1=CC=CC=C1 FTDZECHQBVIHKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 97
- 108091008695 photoreceptors Proteins 0.000 description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000011347 resin Substances 0.000 description 23
- 229920005989 resin Polymers 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 20
- 239000002245 particle Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000010419 fine particle Substances 0.000 description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 238000003384 imaging method Methods 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 11
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 10
- 229910052710 silicon Inorganic materials 0.000 description 10
- 150000003377 silicon compounds Chemical class 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 150000003384 small molecules Chemical class 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000011241 protective layer Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 125000005266 diarylamine group Chemical group 0.000 description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 150000001503 aryl iodides Chemical class 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000008119 colloidal silica Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 239000011354 acetal resin Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052593 corundum Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 229910001845 yogo sapphire Inorganic materials 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- 0 C.[1*]C1=C(Br)C([4*])=C([3*])C(C2=C([8*])C([7*])=C(Br)C([6*])=C2[5*])=C1[2*].[1*]C1=C(N([Ar])[Ar])C([4*])=C([3*])C(C2=C([8*])C([7*])=C(N([Ar])[Ar])C([6*])=C2[5*])=C1[2*].[Ar].[Ar].[Ar]N[Ar] Chemical compound C.[1*]C1=C(Br)C([4*])=C([3*])C(C2=C([8*])C([7*])=C(Br)C([6*])=C2[5*])=C1[2*].[1*]C1=C(N([Ar])[Ar])C([4*])=C([3*])C(C2=C([8*])C([7*])=C(N([Ar])[Ar])C([6*])=C2[5*])=C1[2*].[Ar].[Ar].[Ar]N[Ar] 0.000 description 2
- UJSORZVCMMYGBS-UHFFFAOYSA-N CC12CC3(C)CC(C)(C1)CC(C)(C2)C3 Chemical compound CC12CC3(C)CC(C)(C1)CC(C)(C2)C3 UJSORZVCMMYGBS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- DMDPKUWXJUYFKO-UHFFFAOYSA-N 1,1'-biphenyl;hydrochloride Chemical compound Cl.C1=CC=CC=C1C1=CC=CC=C1 DMDPKUWXJUYFKO-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- GLSRAPNRLWOZMY-UHFFFAOYSA-N 1-phosphatricyclo[3.3.1.13,7]decane Chemical compound C1C(C2)CC3CC1CP2C3 GLSRAPNRLWOZMY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
Definitions
- This disclosure is generally directed to improved chemical processes for the synthesis of arylamine compounds, and to the use of such arylamine compounds in producing electrophotographic imaging members.
- this disclosure provides a method for producing a tetra(aryl)-biphenyldiamine compound by the reaction of a dibromobiphenyl compound with a diarylamine compound from readily available materials.
- the application also discloses a process for forming a siloxane-containing hole-transport molecule, comprising: reacting a dicarboxylic acid of an arylamine compound with an anhydrous alkali earth salt to form an anhydrous dicarboxylic acid salt of the arylamine compound; and reacting the anhydrous dicarboxylic acid salt of the arylamine compound with a siloxane-containing compound.
- JP-A-63-65449 discloses an electrophotographic photoreceptor in which fine silicone particles are added to a photosensitive layer, and also discloses that such addition of the fine silicone particles imparts lubricity to a surface of the photoreceptor.
- JP-B-5-47104 discloses electrophotographic photoreceptors using silicone materials as the binder polymers or the polymer precursors thereof.
- a protective layer is formed on the surface of the photosensitive layer in some cases.
- a cross-linkable resin is used as a material for the protective layer in many cases.
- the protective layer formed by the cross-linkable resin acts as an insulating layer, which impairs the photoelectric characteristics of the photoreceptor. For this reason, a method of dispersing a fine conductive metal oxide powder (JP-A-57-128344) or a charge-transport substance (JP-A-4-15659) in the protective layer and a method of reacting a charge-transport substance having a reactive functional group with a thermoplastic resin to form the protective layer have been proposed.
- a surface of the photoreceptor may become stained with a discharge product produced in contact charging or with polymerization toner that remains after a transport step. This staining, can deteriorate image quality in some cases.
- use of a cleaning blade to remove discharge product or remaining toner adhered to the photoreceptor surface increases friction and abrasion between the surface of the photoreceptor and the cleaning blade, resulting in a tendency to cause damage to the surface of the photoreceptor, breakage of the blade or turning up of the blade.
- the above-mentioned conventional electrophotographic photoreceptor is not necessarily sufficient in electrophotographic characteristics and durability, particularly when such a photoreceptor is used in an environment of high heat and humidity.
- Photoreceptors having low wear rates such as those described in Yamada, also have low refresh rates.
- the low wear and refresh rates are a primary cause of image-deletion errors, particularly under conditions of high humidity and high temperature.
- U.S. Pat. No. 6,730,448 B2 to Yoshino et al. addresses this issue, disclosing photoreceptors having some improvement in image quality, fixing ability, even in an environment of high heat and humidity.
- electrophotographic photoreceptors having high mechanical strength and improved electrophotographic characteristics and improved image deletion characteristics even under conditions of high temperature and high humidity.
- an electrophotographic substrate containing a photoconductive insulating layer on a conductive layer is imaged by first uniformly electrostatically charging a surface of the substrate.
- the substrate is then exposed to a pattern of activating electromagnetic radiation, such as, for example, light.
- the electromagnetic radiation selectively dissipates charge in illuminated areas of the photoconductive insulating layer while leaving behind an electrostatic latent image in non-illuminated areas of the photoconductive insulating layer.
- This electrostatic latent image is then developed to form a visible image by depositing finely divided electroscopic marking particles on the surface of the photoconductive insulating layer.
- the resulting visible image is then transferred from the electrophotographic substrate to a necessary member, such as, for example, an intermediate-transfer member or a print substrate, such as paper.
- a necessary member such as, for example, an intermediate-transfer member or a print substrate, such as paper.
- This image developing process can be repeated as many times as necessary with reusable photoconductive insulating layers.
- image-forming apparatus such as copiers, printers, and facsimiles
- electrophotographic systems in which charging, exposure, development, transfer, etc., are carried out using electrophotographic photoreceptors have been widely employed.
- image-forming apparatus there are ever-increasing demands for speeding up of image-formation processes, improvement in image quality, miniaturization and prolonged life of the apparatus, reduction in production cost and running cost, etc.
- digital systems and color-image output systems have been applied also to the image-forming apparatus.
- Electrophotographic imaging members (such as photoreceptors) are known. Electrophotographic imaging members are commonly used in electrophotographic processes having either a flexible belt or a rigid drum configuration. These electrophotographic imaging members sometimes comprise a photoconductive layer including a single layer or composite layers. These electrophotographic imaging members take many different forms. For example, layered photoresponsive imaging members are known in the art. U.S. Pat. No. 4,265,990 to Stolka et al. describes a layered photoreceptor having separate photogenerating and charge-transport layers. The photogenerating layer disclosed in Stolka is capable of photogenerating holes and injecting the photogenerated holes into the charge-transport layer. Thus, in the photoreceptors of Stolka, the photogenerating material generates electrons and holes when subjected to light.
- a multi-layered photoreceptor employed in electrophotographic imaging systems sometimes includes one or more of a substrate, an undercoating layer, an intermediate layer, an optional hole- or charge-blocking layer, a charge-generating layer (including a photogenerating material in a binder) over an undercoating layer and/or a blocking layer, and a charge-transport layer (including a charge-transport material in a binder). Additional layers such as one or more overcoat layer or layers are also sometimes included.
- arylamine compounds such as N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine compounds that are useful as charge-transport compounds in electrostatographic imaging devices and processes, often involves processes that are costly and/or time-consuming.
- arylamine derivative hole-transporting molecules are prepared by a process that includes an Ullman reaction.
- the Ullman reaction involves the reaction of an aryliodide and an arylamine that includes the use of a copper catalyst that is either ligated or not, in the presence of a base. These reactions are typically carried out for long periods of time, at highly elevated temperatures, and with large amounts of base and catalyst.
- the starting materials can also be very expensive.
- arylamine derivative hole transporting molecules have been prepared by a process that includes a palladium-ligated catalyst in the presence of a base. See, for example, commonly assigned U.S. patent application Ser. No. 10/992,690 filed Nov. 22, 2004.
- a palladium-ligated catalyst in the presence of a base.
- an arylamine derivative can be economically manufactured in a shorter period of time that is isolatable in suitable purity to be used for example, for application in electrophotographic photoreceptors.
- the above-mentioned process has its drawbacks.
- the process typically uses palladium acetate ligated with tri-t-butylphosphine and sodium t-butoxide base as a reaction catalyst. While this scheme greatly reduces the reaction time, tri-t-butylphosphine is expensive and pyrophoric (spontaneously combusts in the presence of air).
- the present disclosure addresses these and other needs, by providing an improved method for the preparation of tetra(aryl)-biphenyldiamine compounds using a ligated palladium catalyst in the presence of base. More particularly, this disclosure provides a method whereby N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamines and arylamine derivatives can be made using an improved reaction that utilizes a ligated palladium catalyst that is better suited for the industrial production of such compounds.
- arylamine compounds including N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine and triarylamine compounds, are further useful in forming various layers suitable for use in imaging members.
- the arylamine compounds can be used as charge transport materials in various layers of an imaging member, including the charge transport layer and the overcoat layer.
- the disclosure provides a process for forming a tetra(aryl)-biphenyldiamine compound, comprising reacting a dibromobiphenyl compound and a diarylamine compound in the presence of a palladium ligated catalyst and a base.
- the disclosure provides a process for forming N,N,N′,N′-tetra-p-tolylbiphenyl-4,4′-diamine, comprising reacting 4,4′-dibromobiphenyl and di-p-toylamine in the presence of a palladium ligated catalyst, wherein the catalyst comprises a palladium acetate ligated with 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane and sodium t-pentoxide base.
- the FIGURE is a schematic cross sectional view showing an embodiment of an electrophotographic photoreceptor of the disclosure.
- hydrocarbon and “alkane” refer, for example, to branched and unbranched molecules having the general formula C n H 2n+2 , wherein n is, for example, a number from 1 to about 100 or more, such as methane, ethane, n-propane, isopropane, n-butane, isobutane, tert-butane, octane, decane, tetradecane, hexadecane, eicosane, tetracosane, and the like.
- Alkanes may be substituted by replacing hydrogen atoms with one or more functional groups.
- aliphatic refers, for example, to straight-chain molecules, and may be used to describe acyclic, unbranched alkanes.
- long-chain refers, for example, to hydrocarbon chains in which n is a number of from about 8 to about 60, such as from about 20 to about 45 or from about 30 to about 40.
- short-chain refers, for example, to hydrocarbon chains in which n is an integer of from about 1 to about 7, such as from about 2 to about 5 or from about 3 to about 4.
- alkyl refers, for example, to a branched or unbranched saturated hydrocarbon group, derived from an alkane and having the general formula C n H 2n+1 , wherein n is, for example, a number from 1 to about 100 or more, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like.
- lower alkyl refers, for example, to an alkyl group of from about 1 to about 12 carbon atoms.
- Halogenated alkyl refers, for example, to an alkyl group in which at least one hydrogen atom, and optionally all hydrogen atoms, is replaced by a halogen atom.
- aryl refers, for example, to a monocyclic aromatic species of about 6 to about 20 carbon atoms or more, such as phenyl, naphthyl, anthrycyl, and the like.
- these groups may be substituted with one or more independently selected substituents, including alkyl, alkenyl, alkoxy, hydroxyl, and nitro groups.
- arylamine refers, for example, to moieties containing both aryl and amine groups.
- exemplary aralkylene groups have the structure Ar—NRR′, in which Ar represents an aryl group and R and R′ are groups that may be independently selected from hydrogen and substituted and unsubstituted alkyl, alkenyl, aryl, and other suitable functional groups.
- triarylamine refers, for example, to arylamine compounds having the general structure NArAr′Ar′′, in which Ar, Ar′ and Ar′′ represent independently selected aryl groups.
- organic molecule refers, for example, to any molecule that is made up predominantly of carbon and hydrogen, such as, for example, alkanes and arylamines.
- heteroatom refers, for example, to any atom other than carbon and hydrogen. Typical heteroatoms included in organic molecules include oxygen, nitrogen, sulfur and the like.
- Alcohol refers, for example, to an alkyl moiety in which one or more of the hydrogen atoms has been replaced by an —OH group.
- lower alcohol refers, for example, to an alkyl group of about 1 to about 6 carbon atoms in which at least one, and optionally all, of the hydrogen atoms has been replaced by an —OH group.
- “Amine” refers, for example, to an alkyl moiety in which one or more of the hydrogen atoms has been replaced by an —NH 2 group.
- the term “lower amine” refers, for example, to an alkyl group of about 1 to about 6 carbon atoms in which at least one, and optionally all, of the hydrogen atoms has been replaced by an —NH 2 group.
- Carbonyl compound refers, for example, to an organic compound containing a carbonyl group, C ⁇ O, such as, for example, aldehydes, which have the general formula RCOH; ketones, which have the general formula RCOR′; carboxylic acids, which have the general formula RCOOH; and esters, which have the general formula RCOOR′.
- derivative refers, for example, to compounds that are derived from another compound and maintain the same general structure as the compound from which they are derived.
- saturated alcohols and saturated amines are derivatives of alkanes.
- homologous refers, for example, to any number of series of organic compounds that have similar chemical properties and that differ by a constant relative molecular mass.
- lower alcohols are a homologous series that includes CH 3 OH, CH 3 CH 2 OH, C 3 CH 2 CH 2 OH, CH 3 (CH 2 ) 2 CH 2 OH, CH 3 (CH 2 ) 3 CH 2 OH and CH 3 (CH 2 ) 4 CH 2 OH, as well as isomers of these molecules.
- saturated refers, for example, to compounds containing only single bonds.
- unsaturated refers, for example, to compounds that contain one or more double bonds and/or one or more triple bonds.
- distillation refers, for example, to the process of boiling a liquid, condensing the vapor and returning the vapor to the original container.
- boiling point refers, for example, to the temperature at which the saturated vapor pressure of a liquid is equal to the external atmospheric pressure.
- standard temperature and “standard pressure” refer, for example, to the standard conditions used as a basis where properties vary with temperature and/or pressure.
- Standard temperature is 0° C.; standard pressure is 101,325 Pa or 760.0 mmHg.
- room temperature refers, for example, to temperatures in a range of from about 20° C. to about 25° C.
- high temperature environment and “high temperature conditions” refer, for example, to an atmosphere in which the temperature is at least about 28 or about 30° C., and may be as high as about 300° C.
- high humidity environment and “high humidity conditions” refer, for example, to an atmosphere in which the relative humidity is at least about 75 or about 80%.
- An improved method for the preparation of tetra(aryl)-biphenyldiamine compounds is to react a dibromobiphenyl and a diarylamine using a ligated palladium catalyst in the presence of a base.
- 4,4′-dibromobiphenyl and diarylamine can be rapidly reacted to form N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine using palladium acetate ligated with 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane, in the presence of sodium t-pentoxide base.
- This reaction proceeds rapidly, in about 1.5 hours, to produce the desired N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine. This shorter, improved process is now described in detail.
- a dibromobiphenyl compound and a diarylamine compound are used as starting materials. Any suitable dibromobiphenyl compound and diarylamine compound can be used, depending upon the desired final product.
- reaction of the present invention including the starting materials and final product, can generally be represented as follows:
- a 4,4′-dibromobiphenyl is reacted with a diarylamine to produce an N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine.
- the 4,4′-dibromobiphenyl may be substituted or unsubstituted.
- the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 which can be the same or different, can be suitably selected to represent hydrogen, a halogen, an alkyl group having from 1 to about 20 carbon atoms, a hydrocarbon radical having from 1 to about 20 carbon atoms, an aryl group optionally substituted by one or more alkyl groups, an alkyl group containing a heteroatom such as oxygen, nitrogen, sulfur and the like having from 1 to about 20 carbon atoms, a hydrocarbon radical containing a heteroatom such as oxygen, nitrogen, sulfur and the like having from 1 to about 20 carbon atoms, an aryl group containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, optionally substituted by one or more alkyl groups, and the like.
- the diarylamine can be any suitable diarylamine, depending upon the desired final product.
- the substituents Ar1 and Ar2 which can be the same or different, can be any known substituted or unsubstituted aromatic component or a substituted or unsubstituted aryl group having from 2 to about 15 conjugate bonded or fused benzene rings and could include, but is not limited to, phenyl, naphthyl, anthryl, phenanthryl, and the like.
- the substituents on the aryl groups, Ar1 and Ar2 can be suitably selected to represent hydrogen, a halogen, an alkyl group having from 1 to about 20 carbon atoms, a hydrocarbon radical having from 1 to about 20 carbon atoms, an aryl group optionally substituted by one or more alkyl groups, an alkyl group containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, having from 1 to about 20 carbon atoms, a hydrocarbon radical containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, having from 1 to about 20 carbon atoms, an aryl group containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, optionally substituted by one or more alkyl groups, and the like.
- each of the Ar1 and Ar2 are p-tolyl groups.
- the diarylamine is di-p-toylamine.
- the final product is an N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine.
- the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 which can be the same or different, can be suitably selected to represent hydrogen, a halogen, an alkyl group having from 1 to about 20 carbon atoms, a hydrocarbon radical having from 1 to about 20 carbon atoms, an aryl group optionally substituted by one or more alkyl groups, an alkyl group containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, having from 1 to about 20 carbon atoms, a hydrocarbon radical containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, having from 1 to about 20 carbon atoms, an aryl group containing a heteroatom such as oxygen, nitrogen, sulfur, and the
- the substituents Ar1 or Ar2 which can be the same or different, can be any known substituted or unsubstituted aryl group such as phenyl, naphthyl, anthryl, phenanthryl, and the like.
- the substituents on the aryl groups Ar1 and Ar2 may be suitably selected to represent hydrogen, a halogen, an alkyl group having from 1 to about 20 carbon atoms, a hydrocarbon radical having from 1 to about 20 carbon atoms, an aryl group optionally substituted by one or more alkyl groups, an alkyl group containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, having from 1 to about 20 carbon atoms, a hydrocarbon radical containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, having from 1 to about 20 carbon atoms, an aryl group containing a heteroatom such as oxygen, nitrogen, sulfur, and the like, optionally substituted by one or more alkyl groups, and the like.
- each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 represent hydrogen and each of Ar1 and Ar2 are p-tolyl groups.
- the diphenylamine is di-p-toylamine.
- the N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine of this formula is N,N,N′,N′-tetra-p-tolylbiphenyl-4,4′-diamine.
- suitable catalysts are those that are known or discovered to be useful for formation of nitrogen-carbon bonds.
- suitable catalysts include ligated palladium catalysts, such as those disclosed by Buchwald et al. and Hartwig et al. (see, e.g., J. Org. Chem. 2000, 65, 5327-5333, the entire disclosure of which is incorporated herein by reference).
- an example of a suitable catalyst is palladium acetate ligated with tri-t-butylphosphine in the presence of a base.
- an example of a suitable catalyst is palladium acetate ligated with a phospha-adamantane molecule given by structural formula (I):
- each X individually represents either CH 2 or an oxygen atom
- Y 1 , Y 2 , Y 3 , and Y 4 each individually represent a substituted or unsubstituted, straight or branched, alkyl, alkenyl, or alkynyl group having from 1 to about 10 carbon atoms, such as from 1 to about 5, or from 1 to about 3 carbon atoms
- Y 5 represents hydrogen, a substituted or unsubstituted alkyl group, or an aryl group.
- One specific molecule given by formula (I) is 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane, which is manufactured as Cytop-216 (Cytec Industries).
- ligands such as any tertiary phosphine ligand such as biaryldialkylphosphine or trialkyl phosphine ligands, could also be used to produce suitable results (from the point of view of conversion and yield), and thus would be suitable to ligate palladium or other metals and thus act as catalysts for the process described in this disclosure.
- Any suitable base may be used in embodiments, such as an alkaline hydroxide or an alkaline alkoxide and the like.
- Exemplary bases that may be used in embodiments include bases having the general formula MOR, in which O is oxygen, M is a metal atom, and R is a hydrogen or an alkyl group.
- M is a metal selected from potassium, sodium, lithium, calcium, magnesium and the like; and R is a hydrogen or a straight or branched alkyl group selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, octyl, decyl and the like.
- Suitable bases include potassium tert-butoxide, sodium tert-butoxide, and sodium tert-pentoxide.
- the reaction can be conducted in continuous mode. However, the reaction may be conducted in batch mode. For example, the reaction can be carried out for a period of from about 30 minutes to about 5 hours or more, such as a reaction time of from about 1 or from about 1.5 to about 2 or about 3 hours.
- the reaction can be carried out in a suitable solvent, such as toluene, decane, other hydrocarbon solvents (either aromatic or saturated hydrocarbons), or mixtures thereof.
- a suitable solvent such as toluene, decane, other hydrocarbon solvents (either aromatic or saturated hydrocarbons), or mixtures thereof.
- the choice of solvent can be decided based on the solubility of the starting materials, intermediates, and final products, and will be readily apparent or within routine experimentation to those skilled in the art. Furthermore the choice of solvent can be decided based on the desired operating temperature range.
- the described process is exothermic and precautions should be taken to ensure that the solvent chosen is capable of dispersing the produced heat by, for example, refluxing and cooling at such a rate so as to control the exotherm.
- the reaction should be conducted under an atmosphere of inert gas (such as nitrogen or argon) so as to preclude deactivation of catalyst or base by oxygen or atmospheric moisture.
- suitable separation, filtration, and/or purification processes can be conducted, as desired to a desired purity level.
- the desired arylamine product can be subjected to conventional organic washing steps, can be separated, can be decolorized (if necessary), treated with known absorbents (such as silica, alumina, and clays, if necessary) and the like.
- the final product can be isolated, for example, by a suitable recrystallization procedure.
- the final product can also be dried, for example, by air drying, vacuum drying, or the like. All of these procedures are conventional and will be apparent to those skilled in the art.
- the arylamine produced by this process can be used as a final product.
- the arylamine can be used as a charge-transport material in an electrostatographic imaging member.
- An exemplary electrostatographic imaging member will now be described in greater detail.
- the FIGURE is a cross-sectional view schematically showing an embodiment of the electrophotographic photoreceptor of the disclosure.
- the electrophotographic photoreceptor 1 shown in the FIGURE is a function-separation-type photoreceptor in which a charge-generation layer 13 and a charge-transport layer 14 are separately provided. That is, an underlayer 12 , the charge-generation layer 13 , the charge transport layer 14 and a protective layer 15 are laminated onto a conductive support 11 to form a photosensitive layer 16 .
- the protective layer 15 contains a resin soluble in the liquid component contained in the coating solution used for formation of this layer and the silicon compound.
- the various layers of the photoreceptor are generally known, and are described in detail in the above-mentioned commonly owned and co-pending
- the photoreceptors can include various layers such as undercoating layers, charge generating layers, charge transport layers, overcoat layers, and the like.
- the charge transport layer generally comprises a charge transporting small molecule dissolved or molecularly dispersed in a film forming electrically inert polymer such as a polycarbonate.
- dissolved as employed herein is defined as forming a solution in which the small molecule is dissolved in the polymer to form a homogeneous phase.
- molecularly dispersed as used herein is defined as a charge transporting small molecule dispersed in the polymer, the small molecules being dispersed in the polymer on a molecular scale. Any suitable charge transporting or electrically active small molecule may be employed in the charge transport layer.
- charge transporting “small molecule” is defined herein as a monomer that allows the free charge photogenerated in the transport layer to be transported across the transport layer.
- Typical charge transporting small molecules include, for example, pyrazolines such as 1-phenyl-3-(4′-diethylamino styryl)-5-(4′′-diethylamino phenyl)pyrazoline, diamines such as N,N′-diphenyl-N,N′-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine, hydrazones such as N-phenyl-N-methyl-3-(9-ethyl)carbazyl hydrazone and 4-diethyl amino benzaldehyde-1,2-diphenyl hydrazone, and oxadiazoles such as 2,5-bis(4-N,N′-diethylaminophenyl)-1,2,4-oxadiazole, stilbenes and the like.
- pyrazolines such as 1-phenyl-3-(4′-diethylamino styryl)-5-(
- Small molecule charge transporting compounds that permit injection of holes from the pigment into the charge generating layer with high efficiency and transport them across the charge transport layer with very short transit times are N,N′-diphenyl-N,N′-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine, N,N,N′,N′-tetra-p-tolylbiphenyl-4,4′-diamine, and N,N′-bis(3-methylphenyl)-N,N′-bis [4-(1-butyl)phenyl]-[p-terphenyl]-4,4′-diamine.
- the hole transport material in the charge transport layer may comprise a polymeric hole transport material or a combination of a small molecule hole transport material and a polymeric hole transport material.
- any suitable electrically inactive resin binder insoluble in the alcohol solvent used to apply an optional overcoat layer may be employed in the charge transport layer.
- Typical inactive resin binders include polycarbonate resin, polyester, polyarylate, polysulfone, and the like. Molecular weights can vary, for example, from about 20,000 to about 150,000.
- Exemplary binders include polycarbonates such as poly(4,4′-isopropylidene-diphenylene)carbonate (also referred to as bisphenol-A-polycarbonate, poly(4,4′-cyclohexylidinediphenylene)carbonate (referred to as bisphenol-Z polycarbonate), poly(4,4′-isopropylidene-3,3′-dimethyl-diphenyl)carbonate (also referred to as bisphenol-C-polycarbonate) and the like.
- Any suitable charge transporting polymer may also be utilized in the charge transporting layer.
- the charge transporting polymer should be insoluble in any solvent employed to apply the subsequent overcoat layer described below, such as an alcohol solvent.
- Any suitable and conventional technique may be utilized to mix and thereafter apply the charge transport layer coating mixture to the charge generating layer.
- Typical application techniques include spraying, dip coating, roll coating, wire wound rod coating, and the like. Drying of the deposited coating may be effected by any suitable conventional technique such as oven drying, infra red radiation drying, air drying and the like.
- the thickness of the charge transport layer is between about 10 and about 50 micrometers, but thicknesses outside this range can also be used.
- the hole transport layer should be an insulator to the extent that the electrostatic charge placed on the hole transport layer is not conducted in the absence of illumination at a rate sufficient to prevent formation and retention of an electrostatic latent image thereon.
- the ratio of the thickness of the hole transport layer to the charge generator layers is desirably maintained from about 2:1 to 200:1 and in some instances as great as 400:1.
- the charge transport layer is substantially non-absorbing to visible light or radiation in the region of intended use but is electrically “active” in that it allows the injection of photogenerated holes from the photoconductive layer, i.e., charge generation layer, and allows these holes to be transported through itself to selectively discharge a surface charge on the surface of the active layer.
- a protective overcoat layer can be provided over the charge transport layer (or other underlying layer).
- Various overcoating layers are known in the art, and can be used as long as the functional properties of the photoreceptor are not adversely affected.
- the overcoating layers of embodiments can be a silicon overcoat layer, which can comprise one or more silicon compounds, a resin, and a charge transport molecule such as an arylamine.
- the resin may be a resin soluble in a liquid component in a coating solution used for formation of a silicon overcoat layer.
- a resin soluble in the liquid component may be selected based upon the kind of liquid component.
- the coating solution contains an alcoholic solvent
- a polyvinyl acetal resin such as a polyvinyl butyral resin, a polyvinyl formal resin or a partially acetalized polyvinyl acetal resin in which butyral is partially modified with formal or acetoacetal
- a polyamide resin a cellulose resin such as ethyl cellulose and a phenol resin
- these resins may be used either alone or as a combination of two or more resins.
- the polyvinyl acetal resin is particularly suitable in embodiments in terms of electric characteristics.
- the weight-average molecular weight of the resin soluble in the liquid component may be from about 2,000 to about 1,000,000, such as from about 5,000 to about 50,000.
- the weight-average molecular weight is less than about 2,000, enhancing discharge gas resistance, mechanical strength, scratch resistance, particle dispersibility, etc., tend to become insufficient.
- the weight-average molecular weight exceeds about 1,000,000, the resin solubility in the coating solution decreases, and the amount of resin added to the coating solution may be limited and poor film formation in the production of the photosensitive layer may result.
- the amount of the resin soluble in the liquid component may be, in embodiments, from about 0.1 to about 15% by weight, or from about 0.5 to about 10% by weight, based on the total amount of the coating solution.
- the amount added is less than 0.1% by weight, enhancing discharge gas resistance, mechanical strength, scratch resistance, particle dispersibility, etc. tend to become insufficient.
- the amount of the resin soluble in the liquid component exceeds about 15% by weight, there is a tendency for formation of indistinct images when the electrophotographic photoreceptor of the disclosure is used at high temperature and high humidity.
- the silicon compound used in embodiments of the disclosure has at least one silicon atom.
- a compound having two or more silicon atoms in its molecule may be used in embodiments.
- the use of the compound having two or more silicon atoms in its molecule allows both the strength and image quality of the electrophotographic photoreceptor to be achieved at higher levels.
- fine particles can also be added to the silicon compound-containing layer.
- the fine particles may be used either alone or as a combination of two or more such fine particles.
- Non-limiting examples of the fine particles include fine particles containing silicon, such as fine particles containing silicon as a constituent element, and specifically include colloidal silica and fine silicone particles.
- Colloidal silica used in embodiments as the fine particles containing silicon in the disclosure is selected from an acidic or alkaline aqueous dispersion of the fine particles having an average particle size of 1 to 100 nm, or 10 to 30 nm, and a dispersion of the fine particles in an organic solvent such as an alcohol, a ketone or an ester, and generally, commercially available particles can be used.
- colloidal silica in a top surface layer of the electrophotographic photoreceptor of embodiments.
- colloidal silica may be included in amounts of from about 1 to about 50% by weight, such as from about 5 to about 30% by weight, based on the total solid content of the top surface layer, in terms of film forming properties, electric characteristics and strength.
- the fine silicone particles used as the fine particles containing silicon in the disclosure are selected from silicone resin particles, silicone rubber particles and silica particles surface-treated with silicone, which are spherical and have an average particle size of from about 1 to 500 mm, such as from about 10 to about 100 nm, and generally, commercially available particles can be used in embodiments.
- the fine silicone particles are small-sized particles that are chemically inactive and excellent in dispersibility in a resin, and further are low in content as may be necessary for obtaining sufficient characteristics. Accordingly, the surface properties of the electrophotographic photoreceptor can be improved without inhibition of the crosslinking reaction. That is to say, fine silicone particles improve the lubricity and water repellency of surfaces of electrophotographic photoreceptors where incorporated into strong crosslinked structures, which may then be able to maintain good wear resistance and stain adhesion resistance for a long period of time.
- the content of the fine silicone particles in the silicon compound-containing layer of embodiments may be from about 0.1 to about 20% by weight, such as from about 0.5 to about 10% by weight, based on the total solid content of the silicon compound-containing layer.
- fine particles that may be used in embodiments include fine fluorine-based particles such as ethylene tetrafluoride, ethylene trifluoride, propylene hexafluoride, vinyl fluoride and vinylidene fluoride, and semiconductive metal oxides such as ZnO—Al 2 O 3 , SnO 2 —Sb 2 O 3 , In 2 O 3 —SnO 2 , ZnO—TiO 2 , Mg—Al 2 O 3 , FeO—TiO 2 , TiO 2 , SnO 2 , In 2 O 3 , ZnO and MgO.
- fine fluorine-based particles such as ethylene tetrafluoride, ethylene trifluoride, propylene hexafluoride, vinyl fluoride and vinylidene fluoride
- semiconductive metal oxides such as ZnO—Al 2 O 3 , SnO 2 —Sb 2 O 3 , In 2 O 3 —SnO 2 ,
- the silicon compound-containing layer of embodiments may contain the resin soluble in the liquid component in the coating solution used for formation of this layer and the silicon compound, thereby improving the dispersibility of the fine particles in the silicon compound-containing layer. Accordingly, the pot life of the coating solution can be sufficiently prolonged, and it becomes possible to prevent deterioration of the electric characteristics.
- plasticizers that may be used in embodiments include, for example, biphenyl, biphenyl chloride, terphenyl, dibutyl phthalate, diethylene glycol phthalate, dioctyl phthalate, triphenylphosphoric acid, methylnaphthalene, benzophenone, chlorinated paraffin, polypropylene, polystyrene and various fluorohydrocarbons.
- the antioxidants may include an antioxidant having a hindered-phenol, hindered-amine, thioether or phosphite partial structure. This is effective for improvement of potential stability and image quality in environmental variation.
- the antioxidants include an antioxidant having a hindered-phenol, hindered-amine, thioether or phosphite partial structure. This is effective for improvement of potential stability and image quality in environmental variation.
- the silicon-containing layer may be from about 2 to about 5 ⁇ m in thickness, such as from about 2.7 to about 3.2 ⁇ m in thickness.
- the electrophotographic photoreceptor of embodiments may be either a function-separation-type photoreceptor, in which a layer containing a charge-generation substance (charge-generation layer) and a layer containing a charge-transport substance (charge-transport layer) are separately provided, or a monolayer-type photoreceptor, in which both the charge-generation layer and the charge-transport layer are contained in the same layer.
- the reaction is filtered while hot to remove insoluble materials. After cooling, the mixture is diluted to 400-500 mL with isopropanol. The resulting precipitate is filtered and washed with 500 mL methanol. The solid is air dried overnight and then placed in 20 ml, toluene and heated to 80-90° C. where 10 g of alumina is added and left between 80-90° C. for 30 minutes. The mixture is filtered while hot. The solution is concentrated to ⁇ 50-75 mL and then diluted to 300 mL with methanol. The resulting precipitate was filtered and pressed dry before drying overnight in a vacuum oven.
- the dry powder is mixed with 2 mass equivalents of Al 2 O 3 and added to a column already containing 3 mass equivalents of Al 2 O 3 .
- Sand is added to the top of the absorbent bed.
- the column is eluted with refluxing heptane ( ⁇ 350-500 mL). On cooling, the product precipitates and is collected by filtration and vacuum dried overnight.
- N,N,N′,N′,-tetra(4-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine is >95.1%.
- HPLC, 1 H NMR and elemental analysis confirm purity at >99.9%. Ashing followed by ICP analysis does not detect any residual palladium present.
Abstract
Description
Thus, in this embodiment, a 4,4′-dibromobiphenyl is reacted with a diarylamine to produce an N,N,N′,N′-tetra(aryl)-1,1′-biphenyl-4,4′-diamine.
in the presence of a base, where each X individually represents either CH2 or an oxygen atom; Y1, Y2, Y3, and Y4 each individually represent a substituted or unsubstituted, straight or branched, alkyl, alkenyl, or alkynyl group having from 1 to about 10 carbon atoms, such as from 1 to about 5, or from 1 to about 3 carbon atoms; and Y5 represents hydrogen, a substituted or unsubstituted alkyl group, or an aryl group. One specific molecule given by formula (I) is 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane, which is manufactured as Cytop-216 (Cytec Industries). However, it will be apparent to those skilled in the art that other ligands, such as any tertiary phosphine ligand such as biaryldialkylphosphine or trialkyl phosphine ligands, could also be used to produce suitable results (from the point of view of conversion and yield), and thus would be suitable to ligate palladium or other metals and thus act as catalysts for the process described in this disclosure.
Claims (18)
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